I have a 98 standard bravo an want to drill a hole in the gimbal ring to except a grease fitting, the main hole would be 1/8 and the gease fitting is 3/16 has anyone performed this and would it weaken the gimbal ring.

Yes i've done it.Remember the hinge pins roll in a fibreglass type bush.This bush is what wears out.You are right lubrication is the way to go.There is even a cast on the gimble where the grease nipple should go.I made new pins like the HP gimbles have.1" bar welded to 3/4" round plate,tapped and bolted that to the gimble ring and drilled out the thread in the helmet and fitted grease nipples.